N-containing secondary compounds

 Those are encountered less commonly in plants

than the phenolics and terpenoids
 Those are important in view of their bioactivity
as drugs and toxins
They are synthesized from aliphatic and
aromatic amino acids
 Aliphatics via TCA cycle
Aromatics via shikimic acid pathway
Classes of N-containing 2o compounds
1. Alkaloids,
2. Cyanogenic glycosides,
3. Glucosinolates,
4. Nonprotein amino acids
 1. ALKALOIDS
 The most important nitrogen containing secondary
products
 They are being found in more than 15,000 compounds
found in 20% of vascular plants.
 Nitrogen is usually part of a heterocyclic ring with N and
C atoms
 ALKALOIDS

 Large pharmacological effects on animals

 Most effective at deterring mammalian herbivores
 Livestock deaths due to over-consumption of alkaloid
containing plants such as lupines and groundsels
 Often alkaloids are used as medicines for humans
 Some examples: morphine, codeine, and scopolamine
 cocaine, nicotine, and caffeine used as stimulants and
sedatives.
Wild tobacco (Nicotiana sylvestrus)

Wild tobacco can “sense”

which herbivore is feeding
on it. It normally produces
nicotine (an alkaloid) in
response to herbivore
feeding. But if nicotine-
tolerant caterpillars are
feeding, the tobacco
produces terpenes instead.
These terpenes can attract
the predators of the
herbivore.
2. CYANOGENIC GLYCOSIDES
1. Release the toxic gas hydrogen cyanide.
2. plants must have enzymes to break down the
compounds and release a sugar molecule
yielding a compound that can decompose to
form HCN.
3. glycosides and enzymes which break them
down are usually spatially separated (in
different cellular compartments or different
tissues)
 Cyanogenic Glycosides
The degradation process is stimulated by
herbivore feeding
 Cyanogenic Glycosides
S. American native peoples eat cassava (Manihot esculenta),
has high levels of cyanogenic glycosides. Chronic cyanide
poisoning are not uncommon.
 3. GLUCOSINOLATES
1. These compounds release volatile defensive
substances, “mustard oils”, (often herbivore
repellents)
2. Plants like cabbage, broccoli, and radishes
(Brassicaceae family) have these.
4. NON-PROTEIN AMINO ACIDS

1. These amino acids are not incorporated into

proteins but instead act as protective
substances
2. can “mistakenly” be incorporated into protein
and therefore resulting in a nonfunctional
protein.
 Functions of Secondary
Metabolites in Plants
1. The secondary metabolites have no function in the physiology of
the plants
2. They are formed as a result of an overspill from the primary
metabolism
3. They make a valuable contribution to the relationship between plant
and their environment
4. Plant utilized secondary metabolites as antibiotics or signaling agent
during the interaction with pathogen (SAR and Agrobacterium)
5. They play an important role in two resistance strategies:
a. structural level, phenyl propanoids are the major
component of wall polymers lignin and suberin
b. Inducible defence antibiotics originated from phenolics,
and terpenoids (phytoalexins)
 Resistance Traits:
Indirect Defense
Induced defenses:
a. Recognition of the pathogen by the host plant;
carbohydrates, fatty acids released by fungi
b. Transmission of alarm signal to host; Ca, hydrogen
peroxide, enzymes.

Herbivore damage can elicit a Signaling Pathway

(Induced Defenses)
Induced structural defenses

cytoplasmic -cytoplasm surrounds hyphae (e.g.,

Armillaria),
 cell wall thickening
 histological (cork layers, adventitious roots),
 abscission layers,
 tyloses and gums,
 necrotic defense (hypersensitive response).
Induced biochemical defenses

 Hypersensitive reactions (phytoalexins, antimicrobials

(important with obligates parasites – rusts, leaf spots,
active oxygen radicals disrupt cell membranes,
reinforcement of host cell walls)
 Antimicrobials – phytoalexins, phenolics
 Immunization
Local and systemic acquired resistance